


Endeavor's With Charles Vane

by PoutyRafeVane1975



Category: Assassin's Creed - All Media Types
Genre: AC4 Black Flag, Blowjobs, F/M, First Time Fingering, NSFW, No Spoilers, One Shot, Oral Sex, Plot What Plot, Porn Without Plot, Smut, Some Fluff, Swearing, Vaginal Fingering, Vaginal Sex, admitting feelings, some teasing, unrequited feelings sort of
Language: English
Status: In-Progress
Published: 2018-09-21
Updated: 2018-09-22
Packaged: 2019-07-15 06:14:58
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 2,844
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16057223
Author URL: https://archiveofourown.org/users/PoutyRafeVane1975/pseuds/PoutyRafeVane1975
Summary: You and Charles Vane (surprise, surprise) have some almost unrequited feelings for one another. He makes you an offer one night that you simply can't resist, plus other factors drive your decision. Things unfold from there, but what kind of things?





	1. Whispers in the Dark

"Spend the night with me, then," spoke the gravelly voiced man, Charles Vane. 

Why had he offered? Simple. You refused to go back home to your parents who did nothing but spew awful words to you. 

You and Vane had known each other since the first day your family set foot on the island of Nassau. Vane was captivated by your beauty, the way you walked sparked something inside of him. There was some unspoken, almost unrequited, feelings between the two of you. It was obvious that something was there, but neither of you had acknowledged it out loud. 

Your breath was shaky as you inhaled and exhaled, unsure of how to answer. Go home with him? Stay at the bar? Go home to your parents? Would they wonder where you were? It doesn't matter; you're an adult, they can go fuck themselves.

"Okay. I'll go home with you." That came out in a near pitiful manner, desperation wavering within your voice. 

He smiled with your answer and led you from the Tavern. 

It was late at night. The streets were empty aside from the drunkards that swayed about while trying to find their way, or held on dearly to a post for support. 

It was odd feeling how much time had flown by in the bar and on the walk to Vane's home. 

He swung the entrance door open and motioned you to go in, him following. 

"It ain't much, but..." his voice was hushed, "It's something." 

You both paused in your footsteps, looking at one another in the dim candle light. 

"I, uh, hope that you don't mind that we gotta share the bed?"

You shook your head with a grin, "That's fine, no problem." 

"Right," he shot you a smile back. 

"I'm going to settle in though, it's late. And you should too." 

You responded, "Yeah. I'll be there in a minute." 

He walked away to the bedroom. You took in your surroundings for a moment before deciding to toss your boots to the side.

It hadn't even been a whole minute until you walked into the room and noticed a shirtless Charles laying on the bed, the covers loosely on his hips.

"You a'right with this?" he smirked.

Your voice was a whisper, "Do what you gotta do." 

You knew that your expression deceived you, your mouth agape for a split second at the sight.

Two could play at this game.

He had his eyes closed, one hand resting under his head, the other on his stomach.

You wiggled out of your skirt, then crawled into bed next to him. You were sure to "accidentally" brush your bare leg against his under the covers.

The sudden touch of your bare skin on- his bare skin?- made his eyes shoot open.

He looked over to you, the blanket showing a good amount of your upper thigh, which his eyes immediately shot to. But he quickly changed his attention to your eyes to not raise your suspicion. Too late. 

You laid on your side, facing him. 

You teased him, his expression still shocked. "Oh, I can cover myself up." Maybe that was a bit too flirty.

Perhaps not.

"Oh no, darlin'. You're fine," he smiled and turned to face you.

You smiled back, "Good night, Charles," you said shortly, turning away from him. Not that he could complain. Your perfect ass was now jutting out, so close to his crotch. 

He laughed under his breath and reached his hand out, taking a hold of your hip, his lips ghosting next to your ear. He gave a small and lonesome thrust to your rear. You felt how hard he already was.

"You're going to do that to me and leave me hangin'?" 

You giggled, "Not exactly."

"Then tell me what you want, Y/N." 

Your neck was exposed so he took this chance to place kisses, a mix of loving and needy, some small pecks and others open mouthed. Oh God, this man was good with his tongue, the way it would sweep a small line up a sensitive spot. The way his lips would tickle you before planting a kiss. The way his facial hair scratched at your soft skin.

"Surprise me," was your answer. You didn't care what this man was going to do to you. All you knew was that you wanted it, whatever it was.

He continued to kiss your neck, speaking through kisses, "You asked for it." 

Charles then snaked his hand from your hip to the waistband of your panties, slowly slipping past it. He brushed your clit lightly repeatedly. 

"You're such a Goddamn tease, Charles," you impatiently spat out.

He huffed through his nose, as if it was a laugh, as he gave your neck one last kiss before pulling away. 

"Get on your back." 

You did as he told you. This made it easier for his fingers to reach down between your soaked lips.

He moaned at the feeling of your wetness as he placed a kiss on your lips. Your hands gripped onto him and you took in the way his muscles tensed under your touch. 

"Are you sure ya want this?"

You nodded to reassure him. 

Without any further hesitation, he pushed a finger inside of you, causing you to moan out. 

"Charles..." you were breathless at the sensation of him being inside of you for the first time. Your eyes fluttered closed as he picked up the pace and hooked his finger more. 

He sat up, removing himself from your grip, and used his free hand to nearly rip your panties off. The sight was fucking gorgeous. 

He continued to work his finger inside of you as he knelt between your legs and enjoyed the way you moved, the way your face told every feeling you felt. He brought his other hand up and rubbed circles around your clit, the sensation making you yelp and jump. You were too cute for him to control a smile from creeping onto his face. 

The finger inside of you picked up speed even more. 

"Fuck!" you yelled, "Keep going!"

He smiled even further, laughing a bit at your command.

"Do you honestly think that I'd start something like this and not let you cum? Come on, Sweetheart," he said, his head dipping low and kissing your lower stomach. "I've been wanting to do this for you for so long."

As if that weren't already obvious, but it was nice to hear it. 

"And I'm not stopping 'til I get every last bit of cum out of ya." 

The mouth on this man was absolute filth, but it got you off even more.

He began to hook his finger violently, constantly brushing against that sensitive bundle of nerves. Your orgasm was coiling up in your stomach. 

Vane gave you teasing kisses down your stomach but stopped at your pubic bone. 

"That's for another time," he confessed. 

The thought of his tongue on your cunt overwhelmed you. You could no longer hold back the force of your orgasm pushing closer. 

One last swipe of his finger against that bundle of nerves, and you were cumming, shouting his name. He continued to finger fuck you throughout your release.

"Charles! Fuck, Charles!" It was the only word you knew at that point, "Charles!!" Your hands searched frantically for something to grab onto, but only found the sheets. That would do. You had a death grip on the sheets as your orgasm rocked through your body. 

This was what you both wanted, for a start. For you to cum on his finger. And, Lord above, forgive you, it was Heavenly.

You hoped that this wouldn't be the last of sexual endeavor's with Charles Vane.


	2. Tell Me Again

**Summary for the Chapter:**

> You can’t help but spend yet another night with Vane.

Another offer, “Stay the night with me.”

“Again?” you asked, “But why?”

His expression showed that he thought you were kidding at first, but he settled for a more serious look instead of joking.

“Darlin’, you were crying when I got here earlier. Your parents are at it again.”

He’s right, but you wouldn’t admit it out loud.

“Vane, do you remember what happened last time?”

He let out a hearty laugh, “And who’s to say that I don’t want that to happen again? ‘F course that’s not the only reason why I want you to spend the night with me again,” his eyes offered some consolation.

You finished off your drink and answered him, “Well, getting the Hell away from my parents does sound pleasant. But what sounds better than that is a good fucking.”

“Oh, don’t get your hopes up. I ain’t fuckin’ you yet,” and he took a sip of his drink.

“But we’re working our way up to that, right?” you winked at him.

He held his tankard up to lips, as if to conceal what he was saying, before he took a sip, “Only if you’re a good girl.” His voice was a low mumble, just hardly audible to your ears.

You couldn’t help yourself. Your body couldn’t resist Charles. You left the bar with him and joined him in his bed.

He hovered over your body as you laid down. His lips slowly traveled your body, slowly starting at your lips, giving you tender kisses. His next destination was your neck. You knew that you’d never tire of the feeling. From there was your collar bone, then your bare chest, then eventually- he stopped, once more at your pubic bone.

You whined in protest.

“I told ya, that’s for another time.”

“But you do want to?” you teased.

He moaned as he laid down next to you and caressed you.

“More than you know. I’m exhausted though, Sweetheart. We can continue this in the morning, if you want?”

You nodded, though a bit saddened. However, you both could use the sleep. Today was one Hell of a day.

You tossed and turned and it felt like an eternity without sleep. Your mind simply couldn’t stop wandering. Charles hadn’t stirred about, but he couldn’t fall asleep either.

You turned over onto your side to face him and began to trace light circles on his toned chest. He opened his eyes at the sudden touch and looked over to you.

“Can I help you?” he asked, his voice deeper than usual. Maybe he was starting to doze off and you had disturbed him.

“I hope that I didn’t bother you,” you explained, “But I can’t sleep.”

He sighed through his nose, “Neither can I.”

Hm. This was a great opening.

He shut his eyes once more but you continued on with your light touches.

“Maybe you could tire me out,” a teasing smile crept onto his face with his devious idea.

“Oh? An’ how would I do that?”

Copying your words from your previous encounter, he said, “Surprise me.”

“Alright.”

With your response, you quickly reached down to his hardening member and began to sluggishly and lightly stroke him. But still, he let out a quiet moan at the touch.

His eyes shot open and looked at your hand working on him. Agonizing. Hell. Beautiful.

“Fuck you,” he whispered out as he let his head fall back onto the pillow, his eyes closing once more as he took in the feeling of your ministrations.

You leaned close to him, next to his ear, and spoke, “Two can play at this game, Captain Vane.”

He grunted with your words and reached his hand down to grab yours, forcing you to grip him harder and to jerk him faster.

You didn’t bother shooing his hand away, no, that would be too easy. You chose the thing that would rile him up even further.

You placed an open mouthed kiss, for the first time, to his neck. You found just the right spot.

His hand stopped and retracted immediately. His arm that was resting on the bed near you reached around you to pull you closer to him. He gripped onto you, wherever he could find, and squeezed. His hands were perfect.

He moaned at the feeling of smooth your lips on his neck, but nearly cried out when you lightly bit down on that sensitive spot at the same time you decided to set a steadier pace with an actual grip.

His eyes remained closed, but he still relished in the feelings you were causing to spark through his body.

You weren’t sure if it’s because of how tired he was, maybe how tired you were, or if he was actually desperate and pathetic for you to just jerk him off. It might have been from the lack of sexual - anything - for a long time.

He begged for it, “Please,” it came out languidly.

Nothing more to say? That’s it? What a shame.

You brought your mouth up to his ear again and told him, “Be a good boy, Charles.”

Little did you know that him, of all people, enjoyed that.

“Be a good boy and beg for me.”

With that, you placed more faint kisses to his neck, not planning on doing anything more rough until he begged you. You had to hear him- a strong man, so commanding, fucking beg.

You gave him one good stroke of pleasure before resuming to your regular, boring pace.

His breath shot out of him and his body jerked with your quick but brief change.

His deep voice groaned out, then he begged, “I’ll be a good boy, Y/N, just- please. Make me cum.” He whined for you to make him cum.

You did as he wished, only slightly. He would have to beg more than that, which he noticed right away.

You were lost in the way he kept his eyes shut, sometimes squeezing them closed tighter as you slicked your hand over his shaft. He didn’t bother gritting his teeth or letting out any growls. It was all desperate.

“Please, Y/N, I’m so fuckin’ desperate for you.”

He opened his eyes and looked into yours. His hand held onto your arm, but you still worked on stroking his hard cock.

“I want you to make me cum. I need you, babygirl. I-” a moan escaped past his lips.

“I…” he hesitated, squinting his eyes closed for a moment.

“I love you.”

He sighed out, relieved that he got it off of his chest, “I fucking love you.”

He moaned, sighed, and cursed at your entire presence. Your essence was enough to drive him wild.

Well, you didn’t expect a confession tonight. More so, Vane didn’t expect your next words.

“I love you too,” and you placed a kiss to his lips, to which he returned without hesitating.

You had the proper grip on his cock, the perfect pace that he loved, all of it was more than enough to make him melt like putty, literally in your hands.

His hips would thrust up for some extra fiction. Each movement of your talented hand earned a wonderful deep grunt from him, still all so needy. Your lips still crashed against each others. He would occasionally breathe out from the ecstatic sensations that were burning within him. All of it made a smile form on your lips, never leaving. He smiled within noticing yours. A continuous smile from the both of you, feeding off of each other in a lovely way.

“You’re such a good boy,” you breathed out.

“I ain’t good for just anyone.”

Oh, you knew.

“And that’s why you’ll be good for me.”

“Don’t test me,” he laughed out, his eyes focusing once more on your hand working on him.

He threw his head back again as you picked up your pace even more.

“Fuck, how are you so good at that?”

You giggled, “It’s the many thoughts I’ve had of doing this to you that prepared me for it.”

He met your movements with his own, continuously thrusting his hips into your hand to work himself even closer to his orgasm.

“I’m so close, Girl. Keep goin’.”

He hesitantly reached a hand down to help you. You dared him to in your mind. But he didn’t.

“You’re doing better than I ever could,” he huffed out, almost embarrassed.

Your lips returned to his neck, which was sure to work him over the edge. It was now your favorite thing to tease him, kiss him, bite and lick at that one spot that drove him fucking nuts on his neck.

“Oh my fuckin’ God.”

And with that, after a few more thrusts, he was cumming. It spurt up and onto his stomach. He grunted like a whore; loud and needy. It was sexy.

He pulled you to him as he was still coming down from his high and feverishly placed his lips to yours.

“Should we clean you up, Charles?”

He nodded as he gathered his breath.

You nuzzled next to him after you had rid him of the mess he made on himself. He welcomed you with an embrace of his own.

“You were such a good boy, Charles.”

Under the dim light, you swore that you saw him blush.


End file.
